Ass Training - my First Challenge

The first, smallest butt plug surprised me when it slid into my tight little rosebud with nary a complaint. I’d been nervous about this exercise and worried that I wouldn’t be able to improve myself for my Master, but there I was with my ass filled for his pleasure. I repeated it every night for the first week, and at the first weekend I was practically smug with how well I had done.

My Master sounded pleased, to be sure, and in that way that he does he allowed himself to think almost out loud. His thoughts culminated with a pleased-sounding “hmmmm…"

“What?” I asked. I knew that “hmmmm…” and often such things were opportunities for me to please him even more. And I can never get enough of such opportunities.

“Well, I was thinking of something, but I’d say its too soon.” He was smiling as he said it, and I took the bait like a prize-winning fish.

“Why? What is it?”

“I have a new task for you,” he smirked over the line, “but it would mean speeding up the process.” I should have considered those words longer, given that at that point I’d only just completed a week of training. But in my mind I was sure I knew his thoughts, and I’d already had the same ones. Rather than waiting another week I would go ahead and jump to the next size of ass plug next week. I was sure I could do it, and in fact was eager to feel myself, my ass, stretching to better myself for his pleasure. So with very little thought I eagerly replied.

“Ok.”

“Ok what?” was his careful response.

“Ok let’s speed up.” I smiled myself this time and I knew he heard it. My ego was about to get me into just a little bit of trouble again.

“Are you sure?” he asked, giving me one last opportunity that I honestly didn’t deserve to reconsider. “Once I tell you there’s no turning back; you’d have to take the challenge.” And of course didn’t take the chance given me.

“I’m sure. What’s the task?”

“On Monday I want you to wear the ass plug to work. All day.”

This was not what I was expecting. I was sure we were talking larger. Not longer. I’d not even kept it in the entire night, so the idea of all day was… daunting. If not a little scary. But I’d asked, and had received my challenge. I knew I’d have no option to reconsider at this point, so I would have to follow through. And though I was scared, I was also excited at such a lofty goal. And I was thrilled at the idea of amusing him. I knew he loved the idea of my working all day long, my mind never off of the tremendous fullness in my ass simply to please him.

On Saturday night I kept the plug in almost all night long; four hours at least I knew. Again my ass happily took the intrusion, and in fact I’d begun to notice pleasure centers in and around my rear. Each time I shoved the plug deep into myself I had a shudder of intense pleasure for a few minutes following. I didn’t know if it was actual, physical pleasure or simply enjoyment of being invaded only to improve myself. And I didn’t really care.

Sunday night as I spoke to him he asked if I was nervous about the next day. I had been thinking about it all day long and confessed to some nerves. This confession only pleased him more. He told me he knew that I’d make him proud; that he had faith in me. So overjoyed was I by his praise I now couldn’t wait for the next morning, when I would fill myself for him. And so it was that 6am the next morning, as the little, black intruder pushed its way into my ass and settled in for the day, that I felt such a rush of excitement and pleasure as to almost cum.

Each step that day was a constant reminder of him. As I sat at my desk I struggled to think about my work, instead fixated on the never ending pressure from the waist down. The experience overloaded my senses and by lunchtime I was incredibly damp between my legs. I went home for lunch, having been given permission by Master to remove it and add more lube. I allowed my tight little hole a rest while I ate my lunch, but when the food was gone I forced myself onto my back, my knees up over my head and my little anal intruder back into its home. As it slid in the second time for that day my rear took it even more readily. In fact, it slid in smoothly, with little of the normal resistance. And once again I was rewarded with a strong ripple throughout my system, bordering on an orgasm.

I had also realized somewhere during my day that I had a business dinner to attend that night. I spoke to Master about how I would be coming home between work and the dinner to be able to talk to him a while, as well as to remove the plug.

“Oh, but what fun would that be?” he asked, that now-familiar smile still in his voice. I assumed that he was kidding, never thinking he would want me to extend my challenge so far. But as I joked back he made himself more clear. “You are to wear the plug through dinner as well, slave.” As is so often the case in these moments I stuttered some kind of resistance while simultaneously loving this sound of his wicked smile and the idea of pleasing him.

The plug stayed with me as I sat at the table of co-workers, making idle chit-chat and privately marveling at what they had no idea about.

That night I was not required to train my ass. As I came home I changed into pj’s and finally removed the plug. My well-worked behind let out its own sigh of relief as it was finally freed from the visitor. Making it that much more surprising the next day at work when I became aware of a new feeling: I missed the plug. My empty ass seemed sad and unchallenged after a day of being to put to work for the sole purpose of amusing its Master. When I trained that night it was a relief to be filled once again. As it is always a relief to be allowed to prove to Master he made the right choice by claiming me oh so many months ago.